WP has the bad habit of disabling the handy flash uploader for people who are on Macs. Annoying, especially if you're dealing with multiple image uploads. Here's how to enable it.
/wp-admin/includes/media.php
Comment out lines 1397 + 1398:
Code:
// if ( false !== stripos($_SERVER['HTTP_USER_AGENT'], 'mac') && apache_mod_loaded('mod_security') )
// $flash = false;
If you wish to protect your WP-Admin via .htaccess and .htpasswd, put this in your .htaccess file within the /wp-admin folder:
Code:
AuthType Basic
AuthName "Protected"
AuthUserFile /path/to/.htpasswd
Require valid-user
# Exclude the file upload and WP CRON scripts from authentication
<FilesMatch "(async-upload\.php|wp-cron\.php|xmlrpc\.php|admin-post\.php)$">
Satisfy Any
Order allow,deny
Allow from all
Deny from none
</FilesMatch>
That will keep your flash uploader from getting stuck after protecting the admin.